Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/418—Amines containing nitro groups
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/10—Preparations for permanently dyeing the hair
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
  • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
  • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
  • C07C215/16—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings

Definitions

• the present invention relates to agents for coloring keratinic fibers containing specific m-phenylenediamine derivatives which carry a linear or branched, chiral or achiral C 5 - to C 8 -monohydroxyalkyl distr, a process for dyeing hair with these agents and some of these m- Phenylenediamine derivatives themselves.
• oxidation dyes For the dyeing of keratin fibers, especially human hair, play the so-called oxidation dyes because of their intense colors and good Fastness properties are a preferred role. Contain such colorants Oxidation dye precursors, so-called developer components and Intermediates.
• the developer components form under the influence of Oxidizing agents or of atmospheric oxygen with each other or under coupling with a or more coupler components, the actual dyes.
• developer components are usually primary aromatic amines with a further, in the para or ortho position, free or substituted hydroxy or Amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives used.
• coupler components are usually m-phenylenediamine derivatives, naphthols, Resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols.
• Coupler substances are in particular 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis- (2,4-diaminophenoxy) -propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol and 2-methyl-4-chloro-5-aminophenol.
• Good oxidation dye precursors are primarily the following prerequisites You must: In the oxidative coupling you have the desired color shades in form sufficient intensity and authenticity. You also need a good one Ownership of the fiber, especially in human hair no noticeable differences between strained and freshly grown Hair may exist (leveling ability). They should be resistant to light, Heat, sweat, friction and the influence of chemical reducing agents, e.g. Perm liquids. Finally, they should - if as hair dyes for Application coming - do not stain the scalp too much, and above all they should be in be toxicologically and dermatologically harmless. Furthermore, the achieved by bleaching can easily be removed from the hair, if it does not correspond to the individual wishes of the individual person and to be reversed.
• Coupler / developer combination usually fails, one on the hair of course to get an effective color nuance. In practice, therefore, are usually Combinations of different developer and / or coupler components used. It There is therefore a constant need for new, improved dye components which are also available in are toxicologically and dermatologically unproblematic.
• Object of the present invention was therefore to new coupler components develop the requirements for oxidation dye precursors, in particular with regard to the toxicological and dermatological properties, fulfill and colorations in a wide color spectrum with good fastness properties enable.
• the coupler components according to the invention make it possible, in particular with p-phenylenediamine and Diaminopyrazolderivaten, good light fastness and a good Leveling.
• a first subject of the present invention are therefore agents for coloring keratinic fibers, in particular human hair, containing in a cosmetically acceptable carrier as coupler component at least one m-phenylenediamine derivative of the formula (I) in which R 1 , R 2 , R 3 and R 4 independently of one another represent a hydrogen atom, a C 1 - to C 4 -alkyl group, a C 2 - to C 4 -monohydroxyalkyl group or R 1 and R 2 or R 3 and R 4 form together with the nitrogen atom carrying them, a pyrrolidine, a piperidine or morpholine ring, with the proviso that one of the substituents R 1 , R 2 , R 3 or R 4 is a linear or branched, chiral or achiral C 5 - to C 8 Monohydroxyalkyl group (X), and R 5 and R 6 independently of one another represent a hydrogen atom, a C 1 - to C 2 -alkyl group, a C 1 -
• keratinic fibers include furs, wool, feathers and especially to understand human hair.
• inventive Oxidation colorants are primarily suitable for dyeing keratin fibers stands in principle a use also in other areas, in particular in the Color photography, nothing contrary.
• m-phenylenediamine derivatives according to the invention are amino compounds act, from these in the usual way, the known Produce acid addition salts. All statements of this document and accordingly the claimed protection scope therefore refer both to the free form present compounds as well as their water-soluble, physiologically acceptable Salts. Examples of such salts are the hydrochlorides, the hydrobromides, the Sulfates, the phosphates, the acetates, the propionates, the citrates and the lactates. The Hydrochlorides and the sulfates are particularly preferred.
• Examples of the C 1 - to C 4 -alkyl groups mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl are preferred alkyl groups. Preferred C 1 to C 2 alkoxy groups are the methoxy and ethoxy groups. Furthermore, as preferred examples of a C 1 to C 4 monohydroxyalkyl group, a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group may be mentioned. A 2-hydroxyethyl group is particularly preferred. The other terms used are derived from the definitions given here.
• the m-phenylenediamine derivatives of the formula (I) can be prepared by conventional produce organic methods. As an example, let's look at the Experimental procedures referenced in the embodiments.
• m-phenylenediamine derivatives of formula (I) are already known in the art. However, it is not apparent from the literature that these can be used as coupler components in hair dyes. Oxidation dye precursors which carry a hydroxyalkyl group having more than 4 carbon atoms are very rarely described in the prior art. Thus, for example, WO-A-93/16 discloses 990 m-phenylenediamine derivatives which have at least one substituent containing a sulfur atom and whose amino groups may be substituted by a C 1 -C 6 -monohydroxyalkyl group. But also in this document only derivatives with short alkyl chains are mentioned as concrete representatives.
• the m-phenylenediamine derivatives be preferred, the at least one asymmetric center in Substituents X have.
• the m-phenylenediamine derivatives of the formula (I) which are described in US Pat This embodiment can be used as a mixture of possible stereoisomers or in the enantiomerically or diastereomerically pure form according to the invention be used. If in the context of this application for m-phenylenediamine derivatives according to formula (I) with at least one asymmetric center no information on stereochemical configuration are made among these compounds their racemates or mixtures of possible stereoisomers to understand.
• the use of the pure stereoisomers of the corresponding m-phenylenediamine derivatives with at least one asymmetric center in the agents according to the invention should also be included.
• substituents X in the context of this embodiment are selected from the group consisting of 1-hydroxy-3,3-dimethylbutan-2-yl, 1-hydroxy-3-methylpentan-2-yl, 1-hydroxy-pentan-2-yl, 1-hydroxy-hexan-2-yl, 1-hydroxy-4-methylpentan-2-yl, 6-hydroxy-6-methyl-heptan-2-yl, 3-hydroxy-2-methyl-hexan-2-yl and 5-hydroxy-2-methylpentan-2-yl, (2R) -1-hydroxy-3,3-dimethylbutan-2-yl, (2S) -1-hydroxy-3,3-dimethylbutane -2-yl, (2R, 3R) -1-hydroxy-3-methylpentan-2-yl, (2S, 3S) -1-hydroxy-3-methylpentan-2-yl, 1-hydroxy-3-methylbutan-2-yl, (2S) -1-hydroxy-3-methylbutan-2-yl, (2R) -1-hydroxy-pentan-2-yl
• the m-phenylenediamine derivatives of the formula (I) which is not an asymmetric center in the substituent X have.
• the substituent X is an unbranched monohydroxyalkyl group. Particular preference is given to the unbranched monohydroxyalkyl groups which have a carry terminal hydroxy group.
• the groups X which are selected are preferred from 5-hydroxypentyl, 6-hydroxyhexyl, 7-hydroxyheptyl, 4-hydroxy-4-methylpentyl, 5-hydroxy-4,4-dimethylpentyl and 3-hydroxy-2,2-dimethyl-propyl.
• Very particularly preferred groups X of this embodiment are the 5-hydroxypentyl group as well as the 6-hydroxyhexyl group.
• the m-phenylenediamine derivatives of the formula (I) may be preferred, in which the nitrogen atom carrying the group X continues to be a hydrogen atom wearing.
• substituents R 1 , R 2 , R 3 and R 4 which do not stand for the groups X stand for a hydrogen atom, a C 1 - to C 2 -alkyl group or a C 2 -Monohydroxyalkyl distr.
• substituents particularly preferably represent a hydrogen atom, a methyl group or a 2-hydroxyethyl group.
• the m-phenylenediamine derivatives of the formula (I) may furthermore be preferred in which R 5 and R 6 independently of one another represent a hydrogen atom, a methyl group, a methoxy group, a hydroxymethyl group or a 2-hydroxyethyl group.
• m-phenylenediamine derivatives of the formula (I) may be preferred in which at least one of R 5 and R 6 is a hydrogen atom.
• Very particularly preferred in the context of this embodiment are the m-phenylenediamine derivatives of the formula (I) in which both radicals R 5 and R 6 are a hydrogen atom.
• m-phenylenediamine derivatives may be preferred in which at least one of R 5 and R 6 is different from a hydrogen atom.
• R 5 or R 6 is a hydrogen atom and the other of R 5 or R 6 is a methyl group.
• the radical other than hydrogen is ortho to both amino groups or para to one of the two amino groups.
• Preferred m-phenylenediamine derivatives of the formula (I) according to the invention are 1- (5-hydroxypentyl) amino-3-aminobenzene, 1- (5-hydroxypentyl) amino-2-methyl-3-aminobenzene, 1- (5-Hydroxypentyl) amino-4-methyl-3-aminobenzene, 1- (5-hydroxypentyl) amino-5-methyl-3-aminobenzene, 1- (5-hydroxypentyl) amino-2-methyl-5-aminobenzene, 1- (6-hydroxyhexyl) amino-3-aminobenzene, 1- (6-hydroxyhexyl) amino-2-methyl-3-aminobenzene, 1- (6-hydroxyhexyl) amino-4-methyl-3-aminobenzene, 1- (6-hydroxyhexyl) amino-5-methyl-3-aminobenzene and 1- (6-hydroxyhexyl) amino-2-methyl-5-aminobenzene.
• particularly preferred m-phenylenediamine derivatives of the formula (I) are 1- (5-hydroxypentyl) amino-3-aminobenzene, 1- (5-hydroxypentyl) amino-2-methyl-3-aminobenzene, 1- (5-Hydroxypentyl) amino-4-methyl-3-aminobenzene, 1- (6-hydroxyhexyl) amino-3-aminobenzene, 1- (6-hydroxyhexyl) amino-2-methyl-3-aminobenzene, and 1- (6-hydroxyhexyl) amino-4-methyl-3-aminobenzo.
• the inventive Colorant also contain at least one developer component.
• developer components are usually primary aromatic amines with a further, in the para or ortho position, free or substituted hydroxy or Amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazole derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives used.
• C 1 - to C 4 -alkyl radicals mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl are preferred alkyl radicals.
• C 1 -C 4 -alkoxy radicals preferred according to the invention are, for example, a methoxy or an ethoxy group.
• a C 1 - to C 4 -hydroxyalkyl group a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group may be mentioned.
• a 2-hydroxyethyl group is particularly preferred.
• a particularly preferred C 2 to C 4 polyhydroxyalkyl group is the 1,2-dihydroxyethyl group.
• halogen atoms are according to the invention F, Cl or Br atoms, Cl atoms are very particularly preferred.
• the other terms used are derived according to the invention from the definitions given here.
• nitrogen-containing groups of the formula (E1) are, in particular, the amino groups, C 1 - to C 4 -monoalkylamino groups, C 1 - to C 4 -dialkylamino groups, C 1 - to C 4 -trialkylammonium groups, C 1 - to C 4 -monohydroxyalkylamino groups, Imidazolinium and ammonium.
• Particularly preferred p-phenylenediamines of the formula (E1) are selected from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2,6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, N, N-dimethyl-p-phenylenediamine, N, N-diethyl-phenylenediamine, N, N-dipropyl-p-phenylenediamine, 4-amino-3-methyl- (N, N-diethyl) -aniline, N, N-bis ( ⁇ -hydroxyethyl) -p-phenylenediamine, 4-N, N-bis ( ⁇ -hydroxyethyl) amino-2-methylaniline, 4-N, N-bis ( ⁇ -hydroxye
• p-phenylenediamine derivatives of the formula (E1) are p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 2- ( ⁇ , ⁇ -dihydroxyethyl) -p-phenylenediamine and N, N-bis ( ⁇ -hydroxyethyl) -p-phenylenediamine.
• a developer component Use compounds containing at least two aromatic nuclei, which with Amino and / or hydroxyl groups are substituted.
• Preferred binuclear developer components of the formula (E2) are in particular: N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol, N, N'-bis ( ⁇ -hydroxyethyl ) -N, N'-bis- (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis (4-methylaminophenyl) tetramethylenediamine, N, N'-diethyl-N, N'-bis (4'-amino-3'-methylphenyl) ethylenediamine, Bis- (2-hydroxy-5-aminophenyl) methane,
• Very particularly preferred binuclear developer components of the formula (E2) are N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol, bis (2-hydroxy-5-aminophenyl) -methane, 1,3-bis- (2,5-diaminophenoxy) -propan-2-ol, N, N'-bis (4'-aminophenyl) -1,4-diazacycloheptane and 1,10-bis (2 ', 5'-diaminophenyl) -1,4,7,10-tetraoxadecane or one of its physiologically acceptable salts.
• Preferred p-aminophenols of the formula (E3) are in particular p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2- ( ⁇ -hydroxyethoxy) -phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethyl-phenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) -phenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol, 4-amino-2-fluorophenol, 4-amino-2-chlorophenol, 4-amino-2,6-dichlorophenol, 4-amino-2- (diethylaminomethyl) -phenol and their physiologically acceptable salts.
• Very particularly preferred compounds of the formula (E3) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol and 4-amino-2- (diethylaminomethyl) phenol.
• the developer component may be selected from o-aminophenol and its Derivatives such as 2-amino-4-methylphenol, 2-amino-5-methylphenol or 2-amino-4-chlorophenol.
• the developer component may be selected from heterocyclic Developer components, such as the pyridine, pyrimidine, pyrazole, pyrazole pyrimidine derivatives and their physiologically acceptable salts.
• heterocyclic Developer components such as the pyridine, pyrimidine, pyrazole, pyrazole pyrimidine derivatives and their physiologically acceptable salts.
• Preferred pyridine derivatives are in particular the compounds described in the patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino-pyridine, 2- (4'-methoxyphenyl) -amino-3-amino-pyridine, 2,3-diamino-6-methoxy-pyridine, 2- ( ⁇ -methoxyethyl) -amino-3-amino-6-methoxy-pyridine and 3,4-diamino-pyridine.
• Preferred pyrimidine derivatives are in particular the compounds described in the German Patent DE 2 359 399, Japanese Laid-Open Patent Publication JP 02019576 A2 or in US Pat Offenlegungsschrift WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine.
• Preferred pyrazole derivatives are in particular the compounds described in the patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, EP-740 931 and DE 195 43 988, such as 4,5-diamino-1-methylpyrazole, 4,5-diamino-1- ( ⁇ -hydroxyethyl) -pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1- (4'-chlorobenzyl) -pyrazole, 4,5-diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl (1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-
• the pyrazolo [1,5-a] -pyrimidines of the above formula (E4) can be used as in Literature described by cyclization starting from an aminopyrazole or Hydrazine be prepared.
• the inventive Colorant at least one further coupler component.
• coupler components are usually m-phenylenediamine derivatives, naphthols, Resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives.
• Coupler substances are in particular 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis- (2 ', 4'-diaminophenoxy) -propane, 2-chloro-resorcinol, 4-chloro-resorcinol, 2-chloro-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcinol and 2-methyl-4-
• coupler components according to the invention are 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 3-aminophenol, 5-amino-2-methylphenol, 2-amino-3-hydroxypyridine, Resorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol and 2,6-dihydroxy-3,4-dimethylpyridine.
• the colorants contain at least one precursor of a naturally-analogous dye.
• Naturally analogous dyes such indoles and indolines are preferably used, the at least one hydroxy or amino group, preferably as a substituent on the six-membered ring, exhibit. These groups may carry further substituents, e.g. B. in the form of a Etherification or esterification of the hydroxy group or alkylation of the amino group.
• the colorants contain at least an indole and / or indoline derivative.
• Particularly suitable precursors of naturally-analogous hair dyes are derivatives of 5,6-dihydroxyindoline of the formula (IIa),
• Particularly preferred derivatives of indoline are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline, 5,6-dihydroxyindoline-2-carboxylic acid and 6-hydroxyindoline, the 6-aminoindoline and the 4-aminoindoline.
• N-methyl-5,6-dihydroxyindoline N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and especially the 5,6-dihydroxyindoline.
• Particularly preferred derivatives of indole are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, 6-hydroxyindole, 6-aminoindole and 4-aminoindole.
• N-methyl-5,6-dihydroxyindole N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole and especially the 5,6-dihydroxyindole.
• the indoline and indole derivatives can be used in the colorants according to the invention both as free bases as well as in the form of their physiologically acceptable salts with inorganic or organic acids, e.g. As the hydrochlorides, sulfates and hydrobromides, be used.
• the indole or indoline derivatives are usually in these Amounts of 0.05-10 wt .-%, preferably 0.2-5 wt .-% included.
• Indoline or indole derivative in colorants in combination with at least one Use amino acid or an oligopeptide is advantageous an ⁇ -amino acid; very particularly preferred ⁇ -amino acids are arginine, ornithine, Lysine, serine and histidine, especially arginine.
• the Colorants according to the invention in a further preferred embodiment of the invention present invention for shading one or more substantive dyes contain.
• Direct dyes are usually nitrophenylenediamines, Nitroaminophenols, azo dyes, anthraquinones or indophenols.
• preferred direct dyes are those under international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange 1, Disperse Orange 3, Acid Orange 7, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 Compounds and 1,4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis ( ⁇ -hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- ( ⁇ -hydroxyethyl) aminophenol, 2- (2'-hydroxyethyl) amino-4,6-dinitrophenol, 1- (2'-hydroxyethyl) amino-4-methyl-2-nitrobenzene,
• Preferred cationic substantive dyes of group (c) are in particular the following compounds:
• the compounds of the formulas (DZ1), (DZ3) and (DZ5), which are also among the Designations Basic Yellow 87, Basic Orange 31 and Basic Red 51 are known very particularly preferred cationic substantive dyes of group (c).
• the cationic substantive dyes under the trademark Arianor® are also very particularly preferred according to the invention cationic substantive dyes.
• the agents according to the invention according to this embodiment contain the direct dyes preferably in an amount of 0.01 to 20 wt .-%, based on the entire colorant.
• preparations according to the invention can also be used in nature occurring dyes such as those in henna red, henna neutral, henna black, chamomile flower, sandalwood, black tea, buckthorn bark, sage, bluewood, Madder root, Catechu, Sedre and Alkana root are included.
• oxidation dye precursors or the direct dyes each represent uniform compounds. Much more can in the hair colorants according to the invention, due to the Production process for the individual dyes, in minor amounts still may contain other components, as far as these are not detrimental to the dyeing result or for other reasons, e.g. toxicological, to be excluded have to.
• Dyes is still expressly referred to the monograph Ch. Zviak, The Science of Hair Care, chapter 7 (pages 248-250, direct dyes) and chapter 8, pages 264-267; Oxidation dye precursors), published as volume 7 of the series "Dermatology" (Ed .: Ch., Culnan and H. Maibach), published by Marcel Dekker Inc., New York, Basel, 1986, as well as the "European Inventory of Cosmetic Raw Materials", published by the European Community, available in disk form from the Federal Association German industrial and trading company for pharmaceuticals, health products and Personal care product e.V., Mannheim, incorporated by reference.
• the colorants according to the invention can furthermore all be known for such preparations Active substances, additives and auxiliary substances.
• the included Colorant at least one surfactant, where in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable. In many cases, however, it has proven to be advantageous to use anionic surfactants, select zwitterionic or nonionic surfactants.
• Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid ,
• Preferred nonionic surfactants are alkyl polyglycosides of the general formula R 1 O- (Z) x . These connections are identified by the following parameters.
• the alkyl radical R 1 contains 6 to 22 carbon atoms and may be both linear and branched. Preference is given to primary linear and methyl-branched in the 2-position aliphatic radicals.
• Such alkyl radicals are, for example, 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. Particularly preferred are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl.
• oxo-alcohols compounds with an odd number of carbon atoms in the alkyl chain predominate.
• the alkyl polyglycosides which can be used according to the invention can contain, for example, only one particular alkyl radical R 1 .
• these compounds are prepared starting from natural fats and oils or mineral oils.
• the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the particular work-up of these compounds.
• sugar building block Z it is possible to use any desired mono- or oligosaccharides.
• sugars with 5 or 6 carbon atoms and the corresponding Used oligosaccharides are, for example, glucose, fructose, Galactose, arabinose, ribose, xylose, lyxose, allose, altrose, mannose, gulose, idose, Talose and sucrose.
• Preferred sugar building blocks are glucose, fructose, galactose, Arabinose and sucrose; Glucose is particularly preferred.
• alkyl polyglycosides which can be used according to the invention contain on average from 1.1 to 5 Sugar units. Alkyl polyglycosides having x values of 1.1 to 1.6 are preferred. All particularly preferred are alkyl glycosides in which x is 1.1 to 1.4.
• the alkyl glycosides can also serve, in addition to their surfactant effect, the fixation to improve fragrance components on the hair.
• the expert will therefore for the Case that over the duration of the hair treatment beyond the effect of Perfume oils on the hair is desired, preferred to this class of substance as resort to further ingredient of the preparations according to the invention.
• alkoxylated homologs of said alkylpolyglycosides can also be used according to the invention be used. These homologs can average up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
• zwitterionic surfactants can be used, in particular as cosurfactants.
• Zwitterionic surfactants are surface-active compounds which carry at least one quaternary ammonium group and at least one -COO (-) or -SO 3 (-) group in the molecule.
• Particularly suitable zwitterionic surfactants are the so-called betaines such as N-alkyl-N, N-dimethylammonium glycinates, for example cocoalkyl dimethylammonium glycinate, N-acylaminopropyl N, N-dimethylammonium glycinates, for example cocoacylaminopropyl-dimethylammonium glycinate, and Alkyl-3-carboxylmethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and Kokosacylaminoethylhydroxyethylcarboxymethylglycinat.
• a preferred zwitterionic surfactant is the fatty acid amide derivative known by the INCI name Cocamidopropyl Betaine.
• ampholytic surfactants are understood as meaning those surface-active compounds which, apart from a C 8 -C 18 -alkyl or acyl group in the molecule, contain at least one free amino group and at least one -COOH or -SO 3 H group and are capable of forming internal salts.
• ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 18 C Atoms in the alkyl group.
• Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12-18 acylsarcosine.
• cationic surfactants in particular those of the type quaternary ammonium compounds, the ester quats and the amidoamines used.
• Preferred quaternary ammonium compounds are ammonium halides, in particular Chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. Cetyltrimethylammonium chloride, Stearyltrimethylammonium chloride, distearyldimethylammonium chloride, Lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, and under the INCI names Quatemium-27 and Quaternium-83 known imidazolium compounds.
• the long alkyl chains of the above surfactants mentioned preferably have 10 to 18 carbon atoms.
• Esterquats are known substances which have at least one ester function and at least one quaternary ammonium group as a structural element.
• Preferred ester quats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized Estersalts of fatty acids with 1,2-Dihydroxypropyldialkylaminen.
• Such products For example, under the trademarks Stepantex®, Dehyquart® and Armocare® distributed.
• alkylamidoamines are usually made by amidation of natural or synthetic Fatty acids and fatty acid sections prepared with dialkylaminoamines.
• An invention particularly suitable compound from this group of substances provides the under the name Tegoamid® S 18 commercially available Stearamidopropyldimethylamin represents.
• cationic surfactants which can be used according to the invention are the quaternized Protein hydrolysates.
• cationic silicone oils such as, for example, commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized Trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing hydroxylamino-modified silicone, also called amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil®-Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quaternium-80).
• a cationic surfactant employable quaternary sugar derivative the commercial product Glucquat®100, according to INCI nomenclature a "Lauryl Methyl Gluceth-10 Hydroxypropyl Dimonium Chloride ".
• the compounds used as surfactant with alkyl groups may be in each case act uniform substances. However, it is usually preferred in the production these substances are based on native plant or animal raw materials, that substance mixtures with different, depending on the respective raw material Alkyl chain lengths.
• the addition products of ethylene and / or propylene oxide with fatty alcohols or derivatives of these addition products can both products with a "normal” homolog distribution as well as those with a narrow homolog distribution be used.
• Under "normal” homolog distribution are thereby Mixtures of homologues understood in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or Alkali metal alcoholates obtained as catalysts.
• Narrow homolog distributions in contrast, obtained when, for example, hydrotalcites, alkaline earth metal salts of Ethercarbonklaren, alkaline earth metal oxides, hydroxides or alkoxides as catalysts be used.
• the use of products with restricted Homolog distribution may be preferred.
• the agents according to the invention preferably contain the dye precursors in one suitable aqueous, alcoholic or aqueous-alcoholic carrier.
• the hair coloring are such carriers, for example, creams, emulsions, gels or surfactant-containing foaming solutions, such as shampoos, Foam aerosols or other preparations intended for use on the hair are suitable.
• the dye precursors in a powdery or to integrate tablet-shaped formulation.
• aqueous-alcoholic solutions are to be understood as meaning aqueous solutions containing from 3 to 70% by weight of a C 1 -C 4 -alcohol, in particular ethanol or isopropanol.
• the compositions according to the invention may additionally contain further organic solvents, for example methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. Preference is given to all water-soluble organic solvents.
• the actual oxidative coloring of the fibers can be done basically with atmospheric oxygen.
• a chemical oxidizing agent is used, especially if, in addition to the coloring, a lightening effect on human hair is desired.
• the oxidizing agents are persulfates, chlorites and in particular hydrogen peroxide or its addition products of urea, melamine and sodium borate in question.
• the oxidation dye can also be used together with a Catalyst can be applied to the hair, the oxidation of the Dye precursors, e.g. by atmospheric oxygen, activated.
• Such catalysts are e.g. Metal ions, iodides, quinones or certain enzymes.
• Suitable metal ions are, for example, Zn 2+ , Cu 2+ , Fe 2+ , Fe 3+ , Mn 2+ , Mn 4+ , Li + , Mg 2+ , Ca 2+ and Al 3+ . Particularly suitable are Zn 2+ , Cu 2+ and Mn 2+ .
• the metal ions can in principle be used in the form of any physiologically acceptable salt or in the form of a complex compound.
• Preferred salts are the acetates, sulfates, halides, lactates and tartrates.
• the actual hair dye is expediently immediately before the Application by mixing the preparation of the oxidizing agent with the preparation, containing the dye precursors.
• the resulting ready-to-use Hair dye preparation should preferably have a pH in the range of 6 to 12 exhibit. Particularly preferred is the application of the hair dye in one weak alkaline environment.
• the application temperatures can be in a range between 15 and 40 ° C lie.
• the Hair dye by rinsing away from the hair to be dyed.
• the preparation with the dye precursors but also without prior mixing with the oxidation component on the Hair will be applied. After an exposure time of 20 to 30 minutes then - optionally after an intermediate rinse - the oxidation component applied. After a further exposure time of 10 to 20 minutes is then rinsed and, if desired shampooed.
• a better Penetration into the hair should cause the appropriate agent to a pH of set about 4 to 7.
• the applied agent preferably has a pH of 7 to 10 having.
• the use acidified peroxydisulfate solutions are preferred as the oxidizing agent.
• a second subject of the present application is the use of M-phenylenediamine derivatives according to the invention for dyeing keratinic fibers.
• a third object of the present invention is a method of dyeing keratinic fibers, in which a hair dye according to the invention on the fibers is applied and rinsed again after a contact time.
• a fourth object of the present invention is N- (6-hydroxyhexyl) -phenylendiamine.
• a fifth subject of the present invention are m-phenylenediamine derivatives of the formula (II) in which R 1 represents a 5-hydroxypentyl group or a 6-hydroxyhexyl group.
• a sixth aspect of the present invention is 3-nitroaniline derivatives of the formula (III) in which R 1 represents a 5-hydroxypentyl group or a 6-hydroxyhexyl group and R 5 represents hydrogen or a methyl group.
• R 1 represents a 5-hydroxypentyl group or a 6-hydroxyhexyl group
• R 5 represents hydrogen or a methyl group.
• the intermediates of the synthesis of the m-phenylenediamines according to the invention selected from the group formed by N- (5-hydroxypentyl) -3-nitroaniline and N- (6-hydroxyhexyl) -3-nitroaniline are particularly preferred.
• a cream base For the preparation of the staining cream, 50 g of a cream base were weighed into a 250 ml beaker and melted at 80 ° C.
• the cream base used had the following composition: Hydrenol® D 17.0% by weight Lorol® tech. 4.0% by weight Texapon® NSO 40.0% by weight Dehyton® K 25.0% by weight Eumulgin® B2 1.5% by weight water 12.5% by weight
• the dissolved dye precursors were sequentially added to the hot cream incorporated. It was then made up to 97 g with distilled water and washed with Ammonia adjusted to a pH of 9.5. After filling up with distilled water 100 g, the batch was stirred cold ( ⁇ 30 ° C), whereby a homogeneous cream was formed.
• dyeing cream for the dyeings, in each case 25 g of dyeing cream were mixed with 25 g of the following oxidizing agent preparation. dipicolinic 0.1% by weight sodium pyrophosphate 0.03% by weight Turpinal® SL 1.50% by weight Texapon® N28 2.00% by weight Acrysol® 22 0.60% by weight Hydrogen peroxide, 50% 12.0% by weight Sodium hydroxide, 45% 0.80% by weight water ad 100% by weight
• One strand of hair (80% gray, 330 mg to 370 mg heavy) was added to each of the mixtures thus obtained. Subsequently, the mixtures and the hair strands were placed on a watch glass and the hair strands well embedded in the dyeing creams. After 30 minutes ( ⁇ 1 minute) exposure time at room temperature, the hair strands were removed and washed with an aqueous Texapon® EVR solution 9 washed so often until the excess color was removed. The strands of hair were air-dried and their color under the daylight lamp (color tester HE240A) determined and noted (Taschenlexikon the colors, A. Kornerup and JH Wanscher, 3rd unchanged edition 1981, MUSTER-SCHMIDT Verlag, Zurich, Göttingen).
• developer component coloration p-toluenediamine sulphate black blue 2,4,5,6-tetra-sulfate Olive p-aminophenol portweinrot 4,5-Dimanio-1- (2-hydroxyethyl) pyrazol-sulfate deep magenta 1- (2-hydroxyethyl) -2,5-p-phenylenediamine sulfate black blue 4-amino-3-methylphenol dun Bis- (2-hydroxy-5-aminophenyl) -methane dihydrochloride dark magenta
• developer component coloration p-toluenediamine sulphate black blue 2,4,5,6-tetra-sulfate Olive p-aminophenol violet brown 4,5-Dimanio-1- (2-hydroxyethyl) pyrazol-sulfate dark magenta 1- (2-hydroxyethyl) -2,5-p-phenylenediamine sulfate black blue 4-amino-3-methylphenol dun Bis- (2-hydroxy-5-aminophenyl) -methane dihydrochloride dark magenta

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